With ubiquitous use of ICT, there are debates whether the research field of Information Systems (IS) is in a crisis. There are increasing number of researchers now arguing for IS research to focus more on ethical agenda and question if we are making this world better with use of ICT. Considering this, the paper explores the nature of relationships between ICT and individuals located on the other side of the digital divide. It is based on a study exploring the use of ICT by teachers based in a developing regional South-Asian Pakistani public university. In this paper, teachers' different ways of interacting with ICT, along with influences of contextual limitations on their daily mundane academic practices are discussed. These contextual socio-economic and technology limitations are affecting damaged teaching experiences and refractive academic practices. The paper elucidates some of the emotional and psychological effects on these individuals due to an uneasy and complex interrelationship of context and action when located on the other side of digital divide. This paper argues that while channelling efforts to establish sound ICT infrastructure is important, engaging and supporting teachers in using ICT to further enrich their professional academics practices could prove beneficial arguably in dealing with issues relating digital gap in a relatively meaningful and sustainable manner.